Fast bases of the triazine series



Patented Sept. 7, 1954 2,688,616 FAST BASES OFCTHE TRIAZINE SERIES Frederick Brody, New York, N. Y., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application March 1, 1952, Serial No. 274,488

3 Claims.

1 The present invention relates to compounds of the formula CtHs in which R is selected from the group consisting of H and RzCO and R and R2 are lower alkyl.

In the past, it has been a considerable problem to obtain azoic coloring matters which have a greenish-blue shade. For the most part, the few coloring matters having the desired shade have been expensive and have had other unsatisfactory characteristics. When the free bases of the present invention, that is to say, where R is hydrogen, are diazotized and coupled with 2- hydroxy-3-naphthoic acid arylides, blue azo coloring matters of a very desirable green shade are obtained, which have good fastness and other properties. The compounds of the present invention are not limited to producing the greenishblue colors, although this is one of their important fields. 0n the contrary, other azocoloring matters of different shades may be obtained by coupling with different coupling components.

The present invention is not limited to any particular method of preparing the compounds, but it has ben found that a very simple method is the condensation of 2,4-diphenyl-6-chloros-triazine with 2,5-dialkoxy-a-amino acyl anilides. The reaction proceeds smoothly and the free bases may be obtained by hydrolyzing oil the acyl roup by conventional means.

It is an advantage of the present invention that the free bases may be readily diazotized and coupled without using any special techniques. For example, azoic pigments may be obtained with various ice-color coupling components; fabrics may be padded with a coupling component and the color developed thereon; or diazoamino, or other stable compounds of the diazos may be prepared and incorporated into azoic printing pastes which are then developed conveniently by acid treatment.

The particular lower alkyl group is not important and may be ethyl, methyl, propyl, or the like. The acyl group may be any of the lower fatty acid acyl groups, such as acetyl, propionyl, and the like. However, because of their cheapness and ready availability, the acetyl compounds are preferred.

Among the typical ice-color coupling compo- NHR nents which may be used in the present invention are compounds such as beta-naphthol; 8-amino- 2-naphthol; 8-acetylamino-2-naphthol, benzyl naphthols, pyrazolones, hydroxybenzofluorenones, and the various N-substituted amides such as arylides of 2-hydroxy-3-naphthoic acid, of 2- hydroxy-3-anthroic acid, of methyl and dimethylsalicylic acids, of hydroxycarbazole carboxylic acids, of hydroxybenzocarbazole carboxylic acids, of hydroxybenzaoridone carboxylic acids, of hydroxydibenzofuran carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoacetic acid, of benzoylacetic acid, and the like.

This invention is further illustrated by the following examples. Where not otherwise specified, parts are by weight.

Example 1 CaHs CZHEO N N NH0 0 CH1 CzHsO Examp e 2 C a I s CaHrL J-NH- N A mixture of 6.02 parts of the above prepared product and 21 parts of concentrated hydrochloric acid in '73 parts of butyl alcohol is refluxed until hydrolysis is complete, cooled, and filtered. The product is obtained in the form of its hydrochloride, which decomposes without melting above 250 C. This reaction can also be run in excellent yield in ethanol instead-of butanol.

The hydrochloride is readily converted to the free base by dissolving in warm pyridine and drowning in water.

Ewamp e 3 05115 CzHxsO QBHEk J-WH on enactm- The above prepared base is diazotized in the ordinary way with hydrochloric acid and sodium nitrite and used to develop cotton cloth padded with 2-hydroxy-3-napthoic anilide. Blue dyeings are obtained of extremely greenish shade, and good fastness properties.

Example 4 4 I claim: 1. A compound of the formula COH R O Celia-k )NH N w in which R is selected from the group consisting of H and- RzCO and R and R2 are lower alkyl.

2. A compound of the formula N N NHCOCH:

CoHr-l )NH N CaHaO 3. A compound of the formula C0115 Q BO N N NE:

C oHs-k )NH- N References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,460,618 Bernasconi Feb. 1, 1949 2,513,264 Hansen June 27, 1950 

1. A COMPOUND OF THE FORMULA 